Anton -- Scheduler doesn't automatically re-submit Plans which fail (except for weather interrupted plans, and that is optional). It does not have a way to decide if a non-weather-safety interrupt is due to clouds, or whatever. So it can't repeatedly re-run Plans that fail. This is by design (in general) because failed plans could accumulate and then repeatedly fail, clogging up the system. The most common cause of a guider failure is missing or too-faint guide star and repeating that plan probably wouldn't help. There are many other failures that would repeat. Trying to tell if a failure would or not repeat would be difficult.

Do you have any source of sky quality? Do you have any people who might be able to set up (script or program) a sky condition input? That would be the way to hint to the Scheduler that the skies aren't good enough.